Water → HCID 57920381, compound

HRID 57162Notes

Reaction equation

HRID 57162 reaction equation
Cl.Cl.[S:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[C:4]1[NH2:12].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[S:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[C:4]1[NH:12][S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 66907004Thieno[2,3-b]pyridin-2-ylamine dihydrochloride

Product 1

HCID 57920381HCID 57920381, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 147-E (0.22 g, 1.00 mmol) in pyridine (5.0 mL) was stirred at rt for 30 min, to which was added benzenesulfonyl chloride (0.135 mL, 1.05 mmol) and the reaction mixture was stirred at rt for 4 h. Another portion of benzenesulfonyl chloride (0.030 mL, 0.235 mmol) was added and the reaction mixture stirred at rt for 72 h. Water and saturated sodium bicarbonate solution were added and the mixture was extracted with dichloromethane, dried over sodium sulfate and evaporated in vacuo to afford a residue.

Workup

  1. stirringthe reaction mixture stirred at rt for 72 h
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customto afford a residue

Sources & evidence

ORD record
ord-36aac68cd4d14e20b90ed0ab76e31cee
Source dataset
uspto-grants-2016_09
Patent number
US09434711B2

Reaction notes

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